Anti-viral triaza compounds

Abstract

A method of inhibiting viruses in which a virus is contacted with an antiviral amount of a compound of formula I. Activity is shown against HIV and other viruses. formula I: <IMAGE> wherein W is a bridge carbon which has a polar or non-polar side group; X and Y independently are an aromatic group or an alkyl group, said aromatic group is selected from the group consisting of Ar, Ar sulfonyl, Ar carboxy and Ar alkyl, where Ar is an aromatic cyclic or aromatic heterocyclic ring having from five to seven members; said alkyl groups having from one to ten carbons; at least one of X and Y is an aromatic group; Z is a group listed for X and Y, a fused aryl moiety having from seven to ten carbons or hydrogen; a, d and e independently are a number from zero to 10; c and b independently are a number from one to 10; and the formula includes sufficient hydrogens for a stable molecule.

What is claimed is: 
     
       1. A method of inhibiting a virus which comprises contacting the virus, a virus-infectable cell or a virus-infected cell with a compound of formula I: ##STR19## wherein W is a bridge carbon which has a polar or non-polar side group; X and Y independently are an aromatic group, an alkyl group, a sulfonyl group or a carbonyl group,   said aromatic group is selected from the group consisting of Ar, Ar sulfonyl, Ar carboxy and Ar alkyl, where Ar has from five to seven ring members and Ar is an aromatic cyclic or aromatic heterocyclic ring;   said alkyl groups having from one to ten carbons;   X and Y are not both an alkyl group;   Z is a group listed for X and Y, a fused aryl moiety having from seven to ten carbons or hydrogen;   a, d and e independently are a number from zero to 10 and when a, d and e are all zero, the compound of formula I is a non-cyclic triamine;   c and b independently are a number from one to ten; and the formula includes sufficient hydrogens for a stable molecule.   
     
     
       2. The method of claim 1 wherein the polar or non-polar side group fox W is selected from the group consisting of double-bonded carbon, double-bonded oxygen, hydroxyl, alkyl of one to about 10 carbons, alkoxy of one to about 10 carbons, aryl of about seven to about 10 carbons, halogen, methyl halogen, methylene halide, epoxide, acyl, CH 2  OH and hydrogen. 
     
     
       3. The method of claim 1 wherein the Ar for X and Y is further substituted with a hydrophilic group. 
     
     
       4. The method of claim 1 wherein the Ar for X and Y is further substituted with NO, NO 2 , NH 2 , NHR, NHR 2 , OH, OR, SH, SR, SOR, SO 2  R, halo, C(halogen) 3 , ##STR20## where R is alkyl of C 1-10 . 
     
     
       5. The method of claim 1 wherein X and Y are independently ##STR21## n=zero to nine R=alkyl of one to 10 carbons R 2  =amino, nitro, sulfhydryl, hydroxy, alkoxy of one to three carbons, acetamino or methyl.   
     
     
       6. The method of claim 1 wherein c and b are three and a, d and e are independently zero or one. 
     
     
       7. The method of claim 1 wherein W is ethene, X and Y are both tosyl and Z is benzyl. 
     
     
       8. The method of claim 1 wherein the compound is 3-Methylene-1,5-ditosyl-1,5,9-triazacyclododecane   9-Benzyl-3-hydroxymethyl-1,5-ditosyl-1,5,9-triazacylododecane   9-Benzyl-3-chloromethyl-1,5-ditosyl-1,5,9-triazacyclododecane   3-Chloromethyl-1,5-ditosyl-1,5,9-triazacyclododecane   N,N-bis (3-toluenesulfonamidopropyl) toluenesulfonamide   
     
     
       1. 5,9-Tritosyl-1,5,9-triazacyclododecane 3-Methylene-1,5,9-tritosyl-1,5,9-triazacyclododecane   3-Hydromethyl-1,5,9-tritosyl-1,5,9-triazacyclododecane   3-Chloromethyl-1,5,9-tritosyl-1,5,9-triazacylododecane   9-Benzyl-3-keto-1,5-ditosyl-1,5,9-triazacyclododecane   9-Benzyl-3-methyl-1,5-ditosyl-1,5,9-triazacyclododecane   9-Benzyl-3-methylene-1,5-ditosyl-1,5,9-triazacyclododecane-9-oxide   9-Acyl-3-methylene-1,5-ditosyl-1,5,9-triazacyclododecane   9-Alkyl-3-methylene-1,5-ditosyl-1,5,9-triazacyclododecane   9-Acyl-3-methylene-1,5-ditosyl-1,5,9-triazacyclododecane epoxide   9-Benzyl-1-formyl-3-methylene-5-tosyl-1,5,9-triazacyclododecane   9-Benzyl-3-methylene-1-tosyl-1,5,9-triazacyclododecane   9-Benzyl-3-methylene-1-acyl-5-tosyl-1,5,9-triazacyclododecane or salts thereof.     
     
     
       9. The method of claim 1 wherein the compound is 9-benzyl-3-methylene-1,5-ditosyl-1,5,9-triazacyclododecane, N-benzylbis(3-toluenesulfonamidopropyl)amine, 3-methylene-1,5-ditosyl-1,5,9-triazacyclododecane or salts thereof. 
     
     
       10. The method of claim 1 wherein the virus is a retrovirus, herpesvirus, influenza virus or rous sarcoma virus. 
     
     
       11. The method of claim 10 wherein the retrovirus is HIV. 
     
     
       12. A method for treating humans or animals suffering from a viral infection comprising administering to said human or animal an antiviral effective amount of a compound of formula I.